Personally, I find the striped down MotoBlur on my old Droid X to be fine, mostly since I turned much of it off. The version on my wifes Droid 3… annoying as hell. But you can fix that yourself later; just root it.
As previously mentioned, the carrier is very important. I went Verizon and have practically always had reception; my friends with other networks are not that lucky. Now, do you want/need a QWERTY keyboard? How important is HDMI? I never plan to hook phone to my TV, so I never use mine. Is 4G speed a must-have, or is plain old 3G good enough?
Pre-loaded apps are a non-issue at best. In fact, the fewer the better since it’s either utter crap or inferior to third-party alternatives. And they all have access to the same markets (plural!), so the only thing you really need to worry about on the software end is which version of Android it has (or, if you plan to root it and go vanilla, which version it supports); you really should shoot for Gingerbread/2.3
@Rarebear Sometimes it’s not a matter of intellect, but rather of patience. In other words, can you learn it before being filled with the urge to murder the damn thing? I lack patience, so much of my knowledge of Gingerbread is useless when using certain phones that run it.